Iodoethane → HCID 22599796, compound

HRID 1592199Notes

Reaction equation

HRID 1592199 reaction equation
[H-].[Na+].[CH2:3]([O:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]([CH:14]([OH:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)[C:4]#[C:5][CH3:6].[CH2:22](I)[CH3:23].[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]([CH:14]([O:21][CH2:22][CH3:23])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]=1)[C:4]#[C:5][CH3:6]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22599869HCID 22599869, compound

Product 1

HCID 22599796HCID 22599796, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 1.5 ml of tetrahydrofuran was suspended 0.05 g of sodium hydride (60% in oil), to which 0.2 g of 6-(2-butynyloxy)-4-(α-hydroxybenzyl)pyrimidine was added under ice cooling, followed by stirring for 15 minutes. Then, 0.2 ml of a tetrahydrofuran solution containing 0.18 g of ethyl iodide was slowly added dropwise, followed by further stirring at the same temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.07 g of 6-(2-butynyloxy)-4-(α-ethoxybenzyl)pyrimidine (the present compound (138)).

Workup

  1. additionwas slowly added dropwise
  2. stirringby further stirring at the same temperature for 2 hours
  3. extractionextracted three times with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8b97d8bdce534efab240123782d52579
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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